close

Вход

Забыли?

вход по аккаунту

?

код для вставки
l’atented use. 17, less
2,412,589
UNirEo' STATES PATENT‘ orrlca
2,412,589
CONDENSATION PRODUCT AND METHOD OF
’
PREPARING AND USING SAME
Eugene Lieber, West New Brighton, N. Y., assign
or to Standard Oil Development Company, a
corporation of Delaware
No Drawing. Application December 19. 1942,
1
Serial No. 469,579
(Cl. 252—59)
' 13 Claims.
.
This invention relates to a novel type of con
2
.
carbon group containing less. than‘ 7_ carbon
densation product and to methods of preparing
atoms. as, for instance, by condensation with
such products and using them for various pur
amyl- chloride. It should be understood that no
invention is claimed herein as to the ?rst step
oi’ either method A or B but only in making the
?nal reaction product. A third method C com
prises simultaneous reaction of all three separate
poses, more particularly as pour depressors in
waxy lubricating oils.
A pour depressor is a substance capable of low-v
ering the temperature at which a hydrocarbon
oil comprising a substantially homogeneous mix
constituents, i. e., ' an aromatic compound, a
ture of liquid hydrocarbons and waxy solids un
resinifying agent capable of resinifying said ara
dergoes loss oi’ ?uidity. The expression "pour 10 maticcompound, and a condensable aliphatic hy
poin ” is used herein to mean the pour point as
drocarbon compound oi low molecular weight,
determined by the standard A. S. T. M. method.
preferably having less than '7 carbon atoms.
Certain heavy-alkyl substituted aromatic hy
That the present invention obtains new and
drocarbon products are mown to be pour depres
unexpected results is clear from. the fact that ,in
sors. It has also been proposed to improve such 15 method A the alkylated aromatic compound to
‘pour depressors by a subsequent resini?cation
be resini?ed does not per se haveany substan
reaction, emphasizing the use of heavy-alkyl sub
tial pour depressing properties, and only attains
stituted aromatics by describing them as being
such properties as a result of the subsequent
made by condensation oi aromatic hydrocarbons
resini?catlon. 0n the other hand, in method B
with “chlorinated aliphatic hydrocarbons oi’ rel 20 the resini?ed aromatic compound ?rst formed is
atively high molecular weight-especially the ,
likewise not a pour depressor and in some cases
- is not ‘even soluble in mineral oil, and the desired
para?ln waxes.” It should be pointed out that
the heavy-alkyl substituted aromatics used as
starting materials in that process are in them
characteristics of suitable oil-solubility and pour
depressing properties are not imparted until the
selves pour depressors for lubricating oils.
25
on the other hand, it has also been suggested
subsequent alkylation.
Another outstanding advantage of the pres
ent invention is that the low molecular weight
aliphatic hydrocarbon compounds used in pre
paring the products of this invention are avail
that pour depressor-s can be prepared by ?rst
resiniiying an aromatic hydrocarbon and then
alhlating the resultant product by condensing
it with chlorinated high molecular weight ali 30 able in large, substantially limitless, quantity
phatic hydrocarbon material such as para?ln wax.
and at relatively low cost: whereas the high mo
It has now been discovered. and is the primary
lecular weight aliphatic compounds used hereto
feature of the present invention, that poweriul
fore are available only in relatively limited quan
and novel wax modifying agents useful particu
titles and at a cost which at times is relatively
larly as pour depressor-s i'or waxy oils can be pre
high, in view of'tbe great demand for such high
pared which comprise essentially a reaction prod
molecular weight products in other ?elds.
uct of an aromatic compound, a resinifying agent
The aromatic compounds to be usedv according
capable of resinifying said aromatic compound,
to the present invention may comprise only one
and a condensable aliphatic hydrocarbon com
or mixtures of a number 01' different types of
pound of low molecular weight preferably having
mono-, di- and other poly-nuclear aromatic hy
drocarbons or hydroxy, amino and other sub
less than '7 carbon atoms. I This result is distinctly
unexpected and contrary to the above and many
other teachings of the prior art.
~ stituted derivatives thereof capable of being re
sini?ed by the resiniiying agents to be mentioned
The purposes of this invention can be accom
plished in several different ways, depending es
further on. Some speci?c examples of suitable
. aromatic compounds are benzene, naphthalene,
sentially upon the order of reacting the several
raw materials. According to one method, which
'for the sake oi’ simplicity will be referred to as
method A, the low molecular weight aliphatic hy-'
anthracene, phenanthrene, di-phenyl, toluene,
phenol, cresol, alpha- and beta-naphthol, ani
line, naphthylamine, and the line.
drocarbon groups are ?rst condensed with an -
aromatic compound to make an alkylated aro
matic compound having at least one alkyl sub
halides, especially the mono-halogen substituted
stituent group containing less than 7 carbon
aliphatic hydrocarbons, or ole?ns corresponding
thereto, such as would be obtained by dehydro
atoms, and subsequently resinifying said prod
uct by treatment with a suitable resinifying
. halogenatlon thereof. Speci?c examples are amyl -
agent, as for instance an aldehyde. On the other '
hand, according to method B. the aromatic com
pound is ?rst resinl?ed, as by reaction with an
aldehyde, and then the resulting product is alkyl
ated with a low molecular weight aliphatic hydro-V
a
The low molecular weight condensable ali
phatichydrocarbon compounds to be used may be
selected ‘from. the group consisting of the aliphatic
chloride, hexyl chloride, butyl chloride, isobutyl
chloride, and even lower alhl halides, such as
the propyl, ethyl and methyl chlorides, although
it is preferred to use those having from 4 to 6
60
carbon. atoms.
2,412,589
Although the halogen substituent is preferably
chlorine from practical considerations, the other
corresponding halides may be used such as bro
mides and iodides, the ?uorides being in most
cases somewhat too stable to give the desired
reaction. Instead of using any single compound.
mixtures of two or more may be used, such as the
mixed amyl chlorides available on the market as
a commercial product, comprising essentially a
mixture of primary, secondary and tertiary amyl
chlorides; or other mixed products such as the
chlorides obtained by simultaneous chlorination
of a mixture of hydrocarbon gases containing
4, 5 and 6 carbon atoms.
The resinifying agents to be used according to
the present invention may be those which are
already known to the art, including Particularly
4
being sufficient in most cases. The amount of
catalyst to be used varies according to the nature
and quantities of reactants used and also depends
to some extent upon the quality and quantity of
product desired, the yield being generally directly
proportional to the amount of catalyst used, up
to a certain optimum amount, decreasing grad
ually therefrom. Sometimes products having the
most potent pour-depressing effects are produced
under conditions giving relatively small yields,
but this is not always true.
By carrying out the invention according to
method B, the aromatic compounds can ?rst be
resini?ed by treating with one of the various
resinifying agents, or others known to the art, and
then the resulting resinous products can be sub
jected to a Friedel-Crafts condensation with a
the aldehydes. such as formaldehyde, or products
lower molecular weight aliphatic hydrocarbon
and the like, or other types of resinifying agents,
such as sulfur halides, elementary sulfur, and so
forth.
In carrying out the invention according to
in the preliminary stage of method A. However,
in method “B,” the alkylation reaction tempera
compound, such as amyl chloride or amylene, in
comprising the same, such as tri—oxymethylene ,
or others such as acetaldehyde, propanaldehyde 20 substantially the same manner as described above
method A,'the alkylated aromatic compound to
be used may either be obtained as such from a
suitable source or may be manufactured especially
for the purposes of this invention, in which case
suitable aromatic compounds, such as those men- ,
tioned above, should be condensed with a suit
. ture should be above 125° F., preferably above
' 150° F., because at lower temperatures the result
ing products are oil-soluble but are not pour
depressors.
~
Particularly in method B, and preferably also
in method A, the. ?nal reaction product is re
covered by distilling oil the low boiling con
30 stituents thereof and from solution in a suitable
inert solvent such as highly re?ned kerosene,
by distillation under reduced pressure, e. g., with
compound, such as amyl chloride or amylene,
?re and steam, or under vacuum at an absolute
preferably by use of a Friedel-Crafts condensing
pressure as low as 100 mm., preferably at low as
agent, e. g., aluminum chloride, boron ?uoride,
zinc chloride, ferric chloride, titanium tetra 35 20 mm. mercury, to about 600° F., leaving as a
distillation residue the desired reaction products
chloride, boron trichloride, and so forth; or, in
able low'molecular weight aliphatic hydrocarbon
some cases anhydrous hydrogen'?uoride or mix
having wax modifying properties.
ably diluted with an inert liquid such as a re?ned
wax modi?er is also useful as a dewaxing aid
The reaction product of. this invention is usually
tures thereof.
Condensations are preferably, although not ' a more or less brittle resin, especially when made
necessarily, carried out in the presence of a solvent 40 by method B, ranging from a yellowish to a dark
brown color, although sometimes it has a greenish
or diluent, such as a refined naphtha or kerosene,
color, and in a few instances it is more of a'vis
or a chlorinated hydrocarbon compound, such
cous oil than a solid.
as tetrachlorethane, dichlorbenzene, or others
The product of this invention has the property
such as carbon disul?de, nitrobenzene, and so
of modifying the crystal structure of waxes such
forth; if a solvent is used, the amount thereof
as para?in wax present when added to composi
should be about one to five times the volume of
tionscontaining same. For instance, when about
the reaction. The temperature should be between
_ .05—10.0%, preferably 02-50%, of this wax modi
the approximate limits of room temperature and
?er is added to a waxy lubricating oil, such as
about 300° F., preferably about 150° to 200° F.
The time of reaction varies inversely with the 50 a Pennsylvania type lubricating oil having a
relatively high pour point, the resultant blend will
temperature used and should be about one-half
have a substantially lower pour point; in other
to five hours, preferably one to two hours.
words, this wax modi?er is an effective pour
After the Friedel-Crafts condensation has been
depressor for waxy oil. A small amount vof this
completed, the reaction mixture is cooled, prefer
for removing wax from mineral lubricating oils
of undesirably high wax content. In similarly
small amounts, this wax modi?er may also be
incorporated into para?in wax or compositions
aromatic compounds as a distillation residue.
' (it) containing the same to be used for various
purposes such as for coating or impregnating
The final resini?cation reaction of method A
paper, etc. or for making various molded products.
is also carried out in the presence of catalysts
The invention will be better understood from
such as sulfuric acid, aluminum chloride, zinc
a consideration of the following examples, which
chloride, acetic acid, phosphoric acid, phosphoric
are given for illustration only.
anyhydride, etc. The use of a solvent or diluent,
as mentioned above in connection with the pre
kerosene, and neutralized by pouring into a mix
ture of alcohol and water. After settling, the
kerosene extract is distilled to remove unreacted
raw materials and to obtain the desired alkylated
liminary Friedel-Crafts condensation. is optional
and preferable, although not necessary. The
resini?cation reaction is also carried out under
‘ approximately the same temperature conditions
as the above Friedel-Crafts condensation, al
though the temperature to be used for optimum
results varies with the nature and amount of the
various reactants being used. The time required
is usually about one-half to two hours, one hour
Mnrnon A
' Example 1
100 grams of mono-amyl naphthalene and 16
grams of trioxymethylene were suspended in 100
cc, of glacial acetic acid and 115 grams of con
centrated sulfuric acid was slowly added to the
reaction mixture with vigorous shaking and cool
ing. After the addition of the sulfuric acid, the
reaction mixture was heated to 122° F. and main
aeraseo "
The procedure for carrying out the reaction
tained thereat for 45 minutes. Water was then
added and the resinous material extracted with
kerosene. After washing, the kerosene extract
and for recovery of product was the same as de
scribed in Example 2._ A bottoms residue com
prising 17 grams of a dark-brown resinous mate
was distilled with fire and steam to 600° F. in or»
der to remove solvent and low-boiling products. $1 rial was obtained as product.
when 1% of this resinification product was
added to a waxy-oil. the pour point of‘ which was
+30° F.. the pour point was found to be —10° 1".
When 5% of this resiniiication product was
When 2 % of this resini?cation product was add
added to a waxy-oil, the pour point of which was
+30" F., the pour point was found to be -15° F. 10 ed to the same waxy-oil a pour point of ~25‘ was
A bottoms residue comprising 84 grams of a green .
viscous oil was obtained as product.
Example 2
100 grams of mono-amyl naphthalene and 16
grams of trioxymethylene were suspended in 100
cc. of a highly pretreated kerosene. 10 grams of
obtained.
.
Mmon B
Example 6
A highly aromatic kerosene is converted to a ,
anhydrous aluminum chloride was then added to
the reaction mixture with ‘suitable agitation.
After the addition of the AlCls, the temperature
clear brittle resinous mass by treatment with
parai'ormaldehyde in the presence of acetic acid
was increased to 175° F. and'maintained thereat
for one hour. After cooling, the reaction mixture
was diluted with 500 cc. further of kerosene and
acid.
50 grams of the kerosene-formaldehyde resin
and a small quantity of concentrated sulfuric 1
was dissolved in 100 cc. of tetrachlorethano as
solvent. To this was added 60 grams of the
mixed amyl chlorides of commerce. 10 grams of
AlCh were now slowly added to the reaction mix
ture with suitable agitation and maintaining the
neutralized by pouring into a mixture of alcohol
and water. After settling, the kerosene extractv
was distilled with fire and steam to 600° F. in or
der to remove solvent and low-boiling products.
A bottoms residue comprising 32 grams of a dark
brown brittle resin was obtained as product.
reaction temperature at 80-90° 1?‘. After the ad
dition of the MCI: the reaction mixture was
heated to 180° F. and maintained thereat for 2
hours. After cooling, the reaction mixture was
When 2% of this resiniflcation product was
added to a waxy-oil, the pour point of which was
+30° E, the pour point was found to be --10° F.
Example 3
v
diluted with kerosene and neutralized with a
30 mixture of alcohol and water. ‘ After settling, the
kerosene extract was distilled with vfire and steam
to 600° F. to remove solvent and low-boiling prod
The following reagents were taken in the pro
portions indicated:
ucts. A bottoms residue, comprising 36 grams of
a dark-green brittle resinous material was ob
'
Mono-amyl naphthalene________ _-grams__
100
Trioxymethylene ________________ .._do__‘.Kerosene as solvent_____‘____ ________ -..cc..A1013 __________________________ _..grams__
16
100
50
" tained as product. It was found to be freely sol
uble in mineral lubricating oil.
The procedure for carrying out the reaction
was the same as described in Example 2.
The 40
product was recovered as before by diluting with
kerosene and neutralizing with a mixture of al.
cohol and water. After settling, the kerosene
extract was distilled with ?re and steam to 600°
F. in order to remove the solvent and low-boiling
When 1% of this condensation product was
addedto a waxy-oil, the pour point of which was
+30° F., the pour point was found to be -15° F.
Example 7 .
The following reagents were'taken in the pro
portions indicated:
_
Grams
Kerosene-formaldehyde resin ____________ __ 50
Mixed amyl chlorides ___________________ __ 120
products. A bottoms residue comprising _61
grams of a dark-brown resinous material was
AlCla --------------------------- _’_ _____ __
obtained as product.
The procedure was the ‘same as described in
When 2% of this resini?cation product was
added to a waxy-oil, the pour point of which was 50 Example 6. Tetrachlorethane was used as sol
+30° E, the pour point was found to be 0° F.‘
Example 4
The following reagents were used in the pro
portions indicated:
.
Mono-amyl naphthalene_-_-_i.----grams__ 100
Trioxymethylene ____ .._>_‘ _________ ..do_.__
A101: _
do
Kerosene as solvent ________________ _..cc_-
16
'80
100
The procedure for carrying out the reaction
‘ and for recovery of product was the same as de
vent.
.
43 grams of a dark-green resinous substance
was obtained as reaction product. It was found
55
to be freely soluble in mineral lubricating oil.
when 1% of this condensation product was
addedto a waxy-oil, the pour point of which. was
+30° R, the pour point was found to be -10° F.
Example 8 '
A naphthalene-formaldehyde resin was pre
pared as follows:
‘
l28grams of naphthalene and 15 grams of
scribed in Example 2.. ‘A bottoms residue com
trioxymethylene weer suspended in 150 cc. of
prising 96 grams of a dark-brown resinous 1
glacial acetic acid. '75 cc. of concentrated sul
terial was obtained as product.
When 2% of this resiniilcation product. was 65 furic acid were slowly added. with suitable agi
tation and cooling to room temperature. After
added to a waxy-oil, the pour point of which was
the addition of the sulfuric acid, the reaction
+30° F., the pour point was found to be --10° F.
mixture was heated to 125-150" F. and main
Example 5
tained thereat for 1 hour.‘ ‘A mixture of water
The following reagents were used in the pro 70 and alcohol was then added and the resinous ma
portions indicated:
terial was extracted with benzene. After wash
Mono-amyl benzene ____________ “gr :n' ..~..
100
ing, the benzene extract was distilled with fire
Trioxymethylene __________________ _-do....
10
and steam to 800° F. to remove solvent and un
Kerosene as solvent................ "0a-;
100
grams
10
reacted naphthalene. A bottoms residue of 80
grams of a clear ‘yellow resinous material was
A1611
aarasee
.
7 ,
parts by weight, or equivalent amounts, of other
obtained as product. This material was found
to be very dimoultly soluble in mineral lubricat
ing oil and to have no pour depressor properties
for waxy oils.
alkyl halides or corresponding olefines.
For the sake of convenience, the experimental
data in Examples 1 to B are summarized in the
50 grams of naphthalene-formaldehyde resin, 5 following table.
‘TABLE
Method A
Resiniiy'ing agt.
I
-
‘
'
Solvent
°F. pour (point
Oat., temp, time
oi’ blen ,'
Test
Alkyl-arom,
130.,
Yield,
No.
name
gm.
gm
Name
1'_ __ Amy] naphtha~
l
10o
e.
Gm
Trioxy-methylene..‘
Name
Go.
1o
Aoeticacid).
10o
16
16
16
10
Kerosene.___
do
._._.d0... ._.
.....d0 ..... __
100
100
100
v100
Gm
msol-.-
° F.
Hrs.
115 .... __
percent added
1
n
2
5
84 .......... ..
-is
’
en
A1011.-. ____ ..
.-_ 0.....
60
.-.do_..__
70
_.
0. __10
175
175
176
175
1
1
l
l
a2
61
96
l7
.... -.
.... __
.... __
—l0
-10
0
—l0
—25
____ _.
.... _.
.... ..
.... ..
Method B
Ammpresm
.
Alkyl
'
Solvent
°F. pour
Cat, temp, time
0! blend):z
Test
Yield,
No.
int
per cent added
gm.
,Name
Gm.
6____ Kgmgene-aromat-
Name
Gm.
Cc.
100
MCI»...
10
100
150
...do._-_.
...do.....
10
10
50
Amylchloride....;..
t0
Tetrachlor-
60
50
_.__.do'. ...... .... i.
----.do ............. --
120
60
_....do...._..
-.-.-do ..... _-
ic formaldehyde.
7____ _____do ___________ __
g____ Naphthalene formaldehyde.
Name
Gm.
ethane.
.
‘’ F.
Bra.
180
2
..
1
36
2
5
-15 __________ __
_
180
180
43 >-10 __________ ,_
to ____ --5 ____ __
2
,
1 Pour point of original oil was 30° F.
Thus according to the present invention, a low
molecular weight alkyl aromatic compound, such
prepared as described above was condensed with
60 grams of mixed amyl chlorides in the presence
of 10 grams of A1013 and using 150 cc. of tetra
chlorethane as solvent. The procedure and re
covery of product was essentially that as de
as amylnaphthalene, which per se has no pour
depressing properties, is converted by resinifica
40 tion as with trioxymethylene, into an active pour
depressor; and similarly, resini?ed aromatic
compounds, e. g., a naphthalene formaldehyde
resin, which per se has little, if any, utility in
lubricating oils, are converted into active pour
scribed in Example 6.
50 grams of a dark resinous material was ob
tained as product. It was found to be freely
soluble in mineral lubricating oil.
-
When 2% of this condensation product was 45 depressors by alkylation with low molecular
added to- a waxy-oil, the pour point of which
weight alkyl groups, such as by condensing with
was +30° F., the pour point was found to be
-5° F.
Other
aromatic
amyl chloride.
hydrocarbon-formaldehyde
resins may be used in place of the resins em- ;
ployed in the examples disclosed above. Thus,
for instance, the formaldehyde resin of anthra
.
i
‘
Method A of this invention and its resulting
product are claimed in application, Ser. No.
354,144, filed August 24, 1940, now issued as Pat-'
ent No. 2,384,107 of September 4, 1945, of which
the present ‘application is a continuation-in-part;
cene, benzene, phenanthrene, ?uorene, diphenyl,
and Method 0, the simultaneous reaction of all .
toluene, xylene, and the like, or the formalde
three constituents and its resulting product are
claimed in co-pending application Ser. No.
hyde resins of mixtures of any of these aromatic _
hydrocarbons may be used, or other aldehyde
resins of naphthalene, or of the aromatic hydro
carbons referred to above, such as naphthalene
acetaldehyde
resins, ‘ anthracene-acetaldehyde
' 469,351, ?led December 1'7, 1942.
It is not intended that this invention be limited
to any of the speci?c examples which were given
merely for the sake of illustration nor to any
resin, etc. may be used, or the corresponding 60 theory as to the mechanism of the operation of
sulfur resins of these same compounds. The
the invention but only by the appended claims
method of preparing these other resins is in
in which it is intended to claim all novelty in
general as described above.
" herent in the invention as broadly as the prior
The proportions in which the various raw ma
, terials should be combined to make the novel
wax modifying agents of this invention, vary to
a substantial extent as indicated in the above
experimental examples, but in general it may be
said that for one mole of aromatic compound,
one-half to five moles of low molecular weight
aliphatic hydrocarbon compounds should be used
and about one-half to two moles of the resinify
ing agent. In Method B for every one part by
weight of resini?ed aromatic compound used, the
amount of alkyl chloride should be about V2 to 3
art permits.
I claim:
1. Process which comprises alkylating a resini
?ed material derived byv resinifying an aromatic
hydrocarbon with an aldehyde, with an alkylating
agent containing less than 7 carbon atoms, at a
temperature aboveabout 125° F., with a Friedel
Crafts catalyst, hydrolyzing and removing the
catalyst and distilling the reaction product under
reduced pressure to about 600° F. to obtain the de
sired product as distillation residue.
75
2.. Process according to claim 1 in which an
2,419,589
9‘
.
aromatic kerosene aldehyde resin is alkylated with
amyl chloride.
.
3. Process of preparing wax modifying agents,
which comprises alkylating about one part by
weight of an aromatic-kerosene formaldehyde
resinywith about 1/2 to 3 parts by weight of amyl
chloride at a temperature of about 125-200° F.‘ in
10
7. A composition comprising a major propor
tion of a hydrocarbon oil and a small but pour
depressing amount of a product de?ned‘ in claim 5.
8. A composition comprising a major propor
tion of a waxy mineral lubricating oil, apour de
pressing amount of a kerosene aromatic-form
aldehyde resin which has been amylated to impart
the presence of aluminum chloride as a catalyst
and in the presence of tetrachlorethane as sol
oil-soluble and pour’depressing properties thereto.
due.
matic hydrocarbon-formaldehyde resin with an
5. Product comprising essentially an oil soluble
resin, substantially non-volatile up to about 600°
alkyl halide having less than 7 carbon atoms at
a temperature above about 125° F. with aluminum
chloride as catalyst, hydrolyzing and removing
the catalyst and distilling the reaction products
9. Process according to claim 1 in which the
vent, for a reaction time of about 1/2 to 5 hours, 10 alkyl group contains 4 to 6 carbon atoms.
hydrolyzing and removing the catalyst and dis
10. Product according to claim 5 m which the '
tilling the reaction products under reduced pres
alkyl group contains 4 to 6 carbon atoms.
11. Process which comprises reacting an arc
sure to about 600° F. to obtain the desired dis
matic hydrocarbon-aldehyde resin with an alkyl
tillation residue having wax modifying proper
ating agent selected from the class consisting of ,
ties.
4. Process which comprises alkylating a naph
alkyl halides and corresponding olefins, having
thalene-formaldehyde resin with at least one
less than 7 carbon atoms, at a temperature above
alkyl group containing less than 7 carbon atoms,
about 125° F. with a Friedel-Crafts catalyst, hy
drolyzlng and removing the catalyst and ‘distilling
at, a, temperature above about 125° F. with a
Friedel-Crafts catalyst, hydrolyzing and remov 20 the reaction products under reduced pressure to
ing the catalyst and distilling the reaction‘ prod
about 600° F. to obtain the desired product as
not under reduced pressure up to about 600° F. to
distillation residue.
.
obtain the desired products as distillation resi
12. Process which comprises reacting an arc
F., and having pour depressing properties, such
product being a resin derived by resini?cation of
an aromatic hydrocarbon by an aldehyde, which
under reduced pressure to about 600° F. to obtain
has been subjected to Friedel-Crafts alkylation 30 the desired product as distillation residue.
at a temperature above about 125° F. with an
13. Process which comprises reacting an aro
alkylating agent containing less than '7 carbon
matic kerosene-formaldehyde resin with an alkyl
atoms.
'
,
6. Product consisting essentially of an oil sol
uble resin, substantially non-volatile up to about
600° F., and having pour depressing properties
when dissolved in waxy mineral lubricating oils
halide having less than '7 carbon atoms at a tem
perature above about 125° F. in the presence of
an inert solvent and with aluminum chloride as
catalyst, hydrolyzing and removing the catalyst
and subjecting the reactionproducts to ?re and
steam distillation up to 600° F. to obtain the de
kerosene formaldehyde resin which has been
sired product as distillation residue.
condensed with amyl chloride at a temperature 40
,
EUGENE LIEBER.
above 125° F.
7 in small amounts, said product being an aromatic
Документ
Категория
Без категории
Просмотров
0
Размер файла
766 Кб
Теги
1/--страниц
Пожаловаться на содержимое документа